Isopropyl iodide → Methyl 2-(4-bromophenyl)-3-methylbutanoate

HRID 1525240노트

반응식

HRID 1525240 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH3:13][C:14]([O-])(C)[CH3:15].[K+].IC(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:14]([CH3:15])[CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6362Isopropyl iodideHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 46855859Methyl 2-(4-bromophenyl)-3-methylbutanoate수율 48%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of methyl 2-(4-bromophenyl)acetate, 13-a, (2.29 g, 10 mmol) in DMF (40 ml) was added dropwise a mixture of t-BuOK (1.12 g, 10 mmol) in DMF (20 mL) with stirring at 0° C. under a nitrogen atmosphere. After stirring at 0° C. for 30 min, 2-iodopropane (1.70 g, 10 mmol) was added dropwise. Then the resulting solution was stirred overnight and ice-water was added. The aqueous layer was extracted by EA. The combined organic layers were washed by brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography to afford the title compound, 13-b, (1.3 g, 48%). 1H NMR (300 MHz, CDCl3) δ 0.70-0.72 (m, 3H), 1.02-1.04 (m, 3H), 2.27-2.32 (m, 1H), 3.10-3.14 (m, 1H), 3.65 (s, 3H), 7.19-7.24 (m, 2H), 7.42-7.45 (m, 2H). LC-MS: (M+H)+ 254, 256.

후처리

  1. stirringAfter stirring at 0° C. for 30 min
  2. stirringThen the resulting solution was stirred overnight
  3. extractionThe aqueous layer was extracted by EA
  4. washThe combined organic layers were washed by brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-0892e3544df246b6b32406941df6b35d
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079930B2

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